A tree sculpture with multiple branches and figures on it, set against a sunset sky with clouds and the ocean in the background.

Diamondhead Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Diamondhead vacation rentals

A corridor leading to a dining area with a view of a green lawn and parked cars.

1. Cozy 1-bedroom condo in lovely Diamondhead with AC

Cozy 1-bedroom condo in lovely Diamondhead with AC
Diamondhead
10.0 out of 10, Exceptional, (3 reviews)
"Clean and cute"
United States
Southern S.
The price is ￥13,212
￥35,736 total
includes taxes & fees
Oct 13 - Oct 14
Cozy 1-bedroom condo in lovely Diamondhead with AC
A kitchen with white cabinets, a coffee maker, and a framed pineapple picture.

2. Relax & Golf - Oakview Condo II at Diamondhead - cozy, new. Walk to the Club

Relax & Golf - Oakview Condo II at Diamondhead - cozy, new. Walk to the Club
Diamondhead
10.0 out of 10, Exceptional, (3 reviews)
"Clean house. Good location. Cheaper than the hotel we originally planned to stay at. I will book again soon and you should too"
United States
Donald W.
The price is ￥14,064
￥44,580 total
includes taxes & fees
Oct 19 - Oct 20
Relax & Golf - Oakview Condo II at Diamondhead - cozy, new. Walk to the Club
A modern kitchen with stainless steel appliances, a large island with bar stools, and a dining area with a view of the outdoors.

3. Upstairs Luxe Style Condo at Diamondhead Country Club - Walk to the Clubhouse

Upstairs Luxe Style Condo at Diamondhead Country Club - Walk to the Clubhouse
Diamondhead
10.0 out of 10, Exceptional, (3 reviews)
"Clean, great communication and a perfect location if you’re golfing in Diamondhead!"
United States
Mackenzie L.
The price is ￥17,758
￥47,058 total
includes taxes & fees
Oct 19 - Oct 20
Upstairs Luxe Style Condo at Diamondhead Country Club - Walk to the Clubhouse
A modern kitchen with a central island, stainless steel appliances, and a dining area with a red chair.

4. Monthly Discount! Near the Golf Course - Diamondhead Country Club at 228Vacay

Monthly Discount! Near the Golf Course - Diamondhead Country Club at 228Vacay
Diamondhead
The price is ￥21,310
￥54,370 total
includes taxes & fees
Oct 19 - Oct 20
Monthly Discount! Near the Golf Course - Diamondhead Country Club at 228Vacay
A room with a large ESPN TV screen, wicker baskets, a wooden table with two red drinks, and a green chair.

5. Cozy 1st Floor Condo /w Full Washer/Dryer - Lacey's Coastal Cabana

Cozy 1st Floor Condo /w Full Washer/Dryer - Lacey's Coastal Cabana
Diamondhead
10.0 out of 10, Exceptional, (14 reviews)
"Perfect spot"
United States
Jennifer H.
Cozy 1st Floor Condo /w Full Washer/Dryer - Lacey's Coastal Cabana
A spacious dining area with a wooden table set for four, white chairs, and a chandelier.

6. 16th and Golden in Diamondhead

16th and Golden in Diamondhead
Diamondhead
9.8 out of 10, Exceptional, (19 reviews)
"Wonderful place to stay for our whole family. We enjoyed the accommodations and especially loved the country club."
United States
Mallory D.
The price is ￥27,447
￥76,859 total
includes taxes & fees
Oct 11 - Oct 12
16th and Golden in Diamondhead
A spacious living room with a brown leather sofa, a round wooden dining table with six chairs, and a large window with blinds.

7. Another Adventure awaits your Arrival. Charming 2 Bed / 2 Bath with Hangar!

Another Adventure awaits your Arrival. Charming 2 Bed / 2 Bath with Hangar!
Diamondhead
10.0 out of 10, Exceptional, (1 review)
"Great host!"
United States
Ben G.
The price is ￥39,463
￥73,813 total
includes taxes & fees
Oct 12 - Oct 13
Another Adventure awaits your Arrival. Charming 2 Bed / 2 Bath with Hangar!
A courtyard with palm trees and string lights, surrounded by a building with a covered patio area.

8. Pass Bungalows

Pass Bungalows
4.5 star property
Pass Christian
9.8 out of 10, Exceptional, (49 reviews)
"The atmosphere was very great. The bungalows were very nice and clean. Only complaint was the pool closing at dark."
United States
Sean
The price is ￥17,756
￥33,147 total
includes taxes & fees
Oct 12 - Oct 13
Pass Bungalows
A cozy living room with a wooden ceiling, a dark leather sofa, a coffee table, and a view through an open doorway to a bedroom.

9. Drackett House by Whiskey Properties

Drackett House by Whiskey Properties
2.5 star property
Old Town Bay St Louis
9.4 out of 10, Exceptional, (43 reviews)
"Good for a quick stay "
United States
CINDY
The price is ￥12,861
￥15,911 total
includes taxes & fees
Nov 1 - Nov 2
Drackett House by Whiskey Properties
A spacious living room with hardwood floors, a brown leather sofa, a recliner, and a spiral staircase.

10. Carroll House Cottages

Carroll House Cottages
3.0 star property
Bay St Louis
9.0 out of 10, Wonderful, (330 reviews)
"The property was clean, quaint and conveniently located near everything. We will be returning in the future."
United States
Carla
The price is ￥14,996
￥32,692 total
includes taxes & fees
Oct 14 - Oct 15
Carroll House Cottages
A dining area with a round wooden table, white chairs, and a vase of flowers. There is a white sofa and a small white table with a lamp. The room has wooden flooring, white walls, and a ceiling with recessed lighting.

11. Cozy 2-bedroom cottage near Bay Saint Louis Harbor

Cozy 2-bedroom cottage near Bay Saint Louis Harbor
Bay St. Louis
10.0 out of 10, Exceptional, (132 reviews)
"Lovely little cottage. Very convenient and very comfortable."
United States
Lisa
The price is ￥10,655
￥32,606 total
includes taxes & fees
Oct 11 - Oct 12
Cozy 2-bedroom cottage near Bay Saint Louis Harbor
A house with a porch, steps, and a small garden area with plants and a potted plant.

12. Quaint Cottage, Walk to Beach and Old Town Bay St. Louis

Quaint Cottage, Walk to Beach and Old Town Bay St. Louis
Bay St Louis
9.8 out of 10, Exceptional, (90 reviews)
"Precious cottage in a wonderful location close to all Old Town BSL has to offer! The host was lovely and helpful. We’ll be back!"
United States
Nanette S.
The price is ￥17,364
￥39,918 total
includes taxes & fees
Oct 14 - Oct 15
Quaint Cottage, Walk to Beach and Old Town Bay St. Louis
A beach house interior with a kitchen, dining area, and a view of the beach.

13. BAY-CAY Getaway, Beaching, Casinos, Swim, Grill, Chill, Memories!

BAY-CAY Getaway, Beaching, Casinos, Swim, Grill, Chill, Memories!
Bay St. Louis
9.8 out of 10, Exceptional, (67 reviews)
"Great place to stay! Convenient to restaurants, buccaneer park, silver slipper casino and much much more! Beautiful view and accommodations!"
United States
lisa c.
The price is ￥18,153
￥36,992 total
includes taxes & fees
Oct 6 - Oct 7
BAY-CAY Getaway, Beaching, Casinos, Swim, Grill, Chill, Memories!
A kitchen with a central island, white cabinetry, and a 'Welcome' sign.

14. Home near white sand beaches and casinos

Home near white sand beaches and casinos
Bay St Louis
10.0 out of 10, Exceptional, (114 reviews)
"Perfect little rental for our couples trip! Great location for golf-carting to town. Paul made sure everything went smoothly, and we had everything we needed."
United States
Jahnele A.
The price is ￥15,485
￥33,568 total
includes taxes & fees
Oct 12 - Oct 13
Home near white sand beaches and casinos
A bedroom with a bed, a ceiling fan, and a window with curtains.

15. Beautiful studio close to the beach!

Beautiful studio close to the beach!
Gulfport
9.2 out of 10, Wonderful, (52 reviews)
"As always, everything was amazing! The apartment is always spotless and the hosts are always super responsive and accommodating!"
United States
Kelsie H.
The price is ￥10,892
￥25,872 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful studio close to the beach!
A two-story house with a covered porch and a small balcony.

16. The Pass Picture Book

The Pass Picture Book
3.0 star property
Pass Christian
10.0 out of 10, Exceptional, (1 review)
The price is ￥22,446
￥25,140 total
includes taxes & fees
Oct 11 - Oct 12
The Pass Picture Book
A two-story wooden structure with a balcony, outdoor seating, and a covered area.

17. New cottage blocks from the beach; pets OK! Firepit! Grill! EV Charger! 65” TV

New cottage blocks from the beach; pets OK! Firepit! Grill! EV Charger! 65” TV
Waveland
10.0 out of 10, Exceptional, (13 reviews)
"Excellent amenities and location. We had a great time and would stay again."
United States
Alex L.
The price is ￥17,364
￥46,284 total
includes taxes & fees
Oct 20 - Oct 21
New cottage blocks from the beach; pets OK! Firepit! Grill! EV Charger! 65” TV
A spacious living room with a neutral color palette, a chandelier, a television, and a kitchen in the background.

18. Beauty and The Bay

Beauty and The Bay
Bay St. Louis
9.4 out of 10, Exceptional, (22 reviews)
"Great place to stay"
United States
Ronnie G.
The price is ￥25,256
￥50,240 total
includes taxes & fees
Oct 19 - Oct 20
Beauty and The Bay
A dining area with a large wooden table, multiple chairs, a chandelier, and artwork on the walls.

19. Old Town Central Station - A home with charm!

Old Town Central Station - A home with charm!
Bay St. Louis
8.4 out of 10, Very good, (32 reviews)
"Loved our stay"
United States
Sheri R.
The price is ￥17,048
￥40,261 total
includes taxes & fees
Oct 19 - Oct 20
Old Town Central Station - A home with charm!
A wooden building with a balcony and a staircase leading to the entrance.

20. J & S's Pond Da Rosa A Place Apart From The Rest

J & S's Pond Da Rosa A Place Apart From The Rest
Bay St. Louis
10.0 out of 10, Exceptional, (16 reviews)
"It was perfect! We will be booking this location every time we go to Bay St. Louis."
United States
Jason M.
The price is ￥27,624
￥63,145 total
includes taxes & fees
Oct 12 - Oct 13
J & S's Pond Da Rosa A Place Apart From The Rest
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Diamondhead Hotel Reviews

Hollywood Casino Gulf Coast

Hollywood Casino Gulf Coast

8/10 Good
"Our rooms thermostat said error and low battery, so no air was moving through the room. It was so stuffy and hot by the time we left I felt miserable. It never got below 75 in there. We did inform the front desk and yet nothing got done. I did also inform the manager today at check out and no courtesy given, just a sly comment about how the maintenance is supposed to follow their orders. the casino wasn’t bad. Lots of variety of games. The lazy river was great and the pool was good. We were a little disappointed how unfriendly the staff came across. Maybe it’s just the culture. This morning when we were getting ready to check out we had a knock on our door from housekeeping asking when we were leaving. It was not even 9am. Luckily I was there to answer the door appropriately. Buffet was average, nothing special. Overall it was an ok hotel, but we probably won’t stay there again."
Shannon 3-night trip
Posted 2 hours ago
Hollywood Casino Gulf Coast

Find out more about Diamondhead

Search for holiday rentals in Diamondhead on Expedia! You can easily find your home rentals, villas, holiday apartments in Diamondhead using one of the methods below:

  • View our selection of featured holiday rentals in Diamondhead
  • Use the map to find apartments and other holiday homes in the Diamondhead neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Diamondhead while they last

Look no further and take a look at our great range of rental properties in Diamondhead!

Frequently asked questions

Are there vacation rentals in Diamondhead?

Yes, you can find vacation rentals near popular attractions in Diamondhead, or you can select a more secluded option if you'd like a relaxing place to stay. Diamondhead is known for its casinos and seafood restaurants. Make sure you have time to check out the golf courses and coffeehouses during your trip.

What's the top vacation rental in Diamondhead?

Drackett House by Whiskey Properties: This vacation home rental near Diamondhead is located in the historical district and has an outdoor pool, a terrace, and free WiFi to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. You can relax into your vacation with a private yard and a hot tub.

How many vacation rentals are there in Diamondhead?

Choose from 17 Expedia vacation rentals in Diamondhead for a memorable vacation.

What’s there to see and do in Diamondhead?

Enjoy the area's cultural attractions such as Thou Art Gallery & GIfts, or get outdoors into nature at a spot like Gulfport SportsPlex. In the larger area, you’ll find Diamondhead Country Club and Hollywood Casino.

What’s a vacation rental in Diamondhead like?

A vacation rental is a private property where you can stay for several days or longer in Diamondhead. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.